Single Family Homes For Sale in Chestertown, MD
46 homes
- AUCTION7 ACRES
- 3D VIEW1.42 ACRESLong & Foster Real Estate, Inc.
- OPEN SAT, 11-2PM3D VIEWDoug Ashley Realtors, LLC
- 0.43 ACRESThurston Wyatt Real Estate, LLC
- COMING SOON 11/27NEW CONSTRUCTIONKevin Dey Realty
- 3D VIEW2.02 ACRESRE/MAX Advantage Realty
- $419,990+4 Beds3.5 Baths2,397 sqftAllegheny | Finished Basement Plan in Radcliffe Meadows,
Chestertown, MD 21620 - $449,990+4 Beds2.5 Baths3,133 sqftColumbia | Finished Basement Plan in Radcliffe Meadows,
Chestertown, MD 21620 - Benson & Mangold, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Doug Ashley Realtors, LLC
- Doug Ashley Realtors, LLC
- Cross Street Realtors LLC
- Douglas Realty LLC
- Coldwell Banker Chesapeake Real Estate Company
- $484,990+3 Beds2.5 Baths3,176 sqftAnderson | Finished Basment Plan in Radcliffe Meadows,
Chestertown, MD 21620 - $439,990+3 Beds2 Baths2,346 sqftAlberti Ranch | Finished Basement Plan in Radcliffe Meadows,
Chestertown, MD 21620 - $464,990+3 Beds2 Baths2,642 sqftBramante Ranch | Finished Basement Plan in Radcliffe Meadows,
Chestertown, MD 21620 - $499,990+3 Beds3 Baths3,301 sqftBramante 2-Story | Finished Basement Plan in Radcliffe Meadows,
Chestertown, MD 21620 - RE/MAX Advantage Realty
- Chesapeake Real Estate Associates, LLC
- Cross Street Realtors LLC
- Benson & Mangold, LLC
- Coldwell Banker Chesapeake Real Estate Company
- Doug Ashley Realtors, LLC
- Cross Street Realtors LLC
- TTR Sotheby's International Realty
- Chesapeake Real Estate Associates, LLC
- Elevated Real Estate Solutions
- Gunther-McClary Real Estate
- Chesapeake Real Estate Associates, LLC
- Coldwell Banker Chesapeake Real Estate Company
Save Search in Chestertown, MD
ChestertownHouseGet emails when new homes match this search

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement.
Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 Bright MLS, Inc. Click here for more information